Of the second month: Hence, you say that they spent twelve months minus ten days at Horeb, for on the first day of [the month of] Sivan, they encamped there, and did not travel until the twentieth of Iyyar of the following year.

The Tabernacle was dismantled: Once the banner of Judah had set out, Aaron and his sons went in, took down the parocheth curtain and covered the Ark with it, as it says, “When the camp is about to travel, Aaron and his sons shall come” (4:5). The sons of Gershon and the sons of Merari dismantled the Tabernacle and loaded it on wagons. The Ark and the holy utensils, which were carried by the sons of Kohath, stood covered and were placed on poles, until the banner of the camp of Reuben set out. Following this,“the Kohathites… set out” (verse 21).

And they had erected the Tabernacle: The sons of Gershon and the sons of Merari, who had preceded them [the Kohathites] by the departure of two banners [their own and Reuben’s], erected the Tabernacle as soon as the cloud settled. The signal for camping was seen in the camp of Judah, and when they encamped, the sons of Kohath were still traveling behind them, with the last two banners [Ephraim and Dan]. The sons of Gershon and Merari erected the Tabernacle so that when the sons of Kohath arrived, they found it set up. They brought in the Ark, the Table, the Candelabrum and the altars. This is the meaning of the verse: Those who erected the Tabernacle erected it עַד, [that is,] before the arrival of the Kohathites.

The collector for all the other camps: The Jerusalem Talmud [states]: Because the tribe of Dan was numerous they traveled last, and if anyone had lost anything, they would [find it and] return it to him. There is an opinion that they traveled in box-like formation, and he derives this from the [the words], “Just as they camp so shall they travel” (2:17). Another opinion is that they traveled in the form of a beam, and he derives this from [the words], “collector for all the camps.”

26Heading the legion of the tribe of the children of Asher was Pagiel the son of Ocran.

כווְעַ֨ל־צְבָ֔א מַטֵּ֖ה בְּנֵ֣י אָשֵׁ֑ר פַּגְעִיאֵ֖ל בֶּן־עָכְרָֽן:

27Heading the legion of the tribe of the children of Naphtali was Ahira the son of Enon.

כזוְעַ֨ל־צְבָ֔א מַטֵּ֖ה בְּנֵ֣י נַפְתָּלִ֑י אֲחִירַ֖ע בֶּן־עֵינָֽן:

28These are the travels of the children of Israel according to their legions, and then they traveled.

כחאֵ֛לֶּה מַסְעֵ֥י בְנֵֽי־יִשְׂרָאֵ֖ל לְצִבְאֹתָ֑ם וַיִּסָּֽעוּ:

These are the travels: This is the order in which they traveled.

אלה מסעי: זה סדר מסעיהם:

And then they traveled: On that day they set out.

ויסעו: ביום ההוא נסעו:

29Then Moses said to Hobab the son of Reuel the Midianite, Moses's father-in-law, We are traveling to the place about which the Lord said, I will give it to you. Come with us and we will be good to you, for the Lord has spoken of good fortune for Israel.

Hobab: This is Jethro, as it says, “Of the children of Hobab, the father-in-law of Moses” (Jud. 4:11). So what does Scripture mean by saying,“They [the daughters of Jethro] came to their father Reuel” (Exod. 2:18)? It teaches that children call their grandfather, ‘father.’ He had many names: 'Jethro’-because through him a portion was added (יֶתֶר) to the Torah; 'Hobab’-because he loved (חֹבָב) the Torah, etc…. [see commentary to Exodus 18:1].

We are traveling to the place: Immediately, within three days, we will enter the Land. For on this first journey they traveled with the intention of entering the Land of Israel, but [because] they sinned at the episode of the complainers [they were punished and did not enter the Land until much later]. Why did Moses include himself with them [if he wasn’t going to enter the Land]? Because the decree against him [entering the Land] had not yet been issued, and [at that time] he thought he would enter.

Please don’t leave us: The word נָא is an expression denoting a request. [He made] this [request] as he didn’t want people to say:“Jethro did not convert out of commitment [for Judaism]; rather, he [thought that proselytes have a portion in the Land. Now that he realizes that they have no portion, he has forsaken them and gone his own way.” - [from Sifrei]

For because you are familiar with our encampments in the desert: It is fitting for you to do this [i.e., remain with us] since you are familiar with the places in which we will camp in the desert and you saw the miracles and wonders done for us.

For because you are familiar…: [The expression… כִּי עַל כֵּן] has the meaning of עַל אֲשֶׁר יָדַעְתָּ, [because you know], as in,“because (כִּי עַל כֵּן) I did not give her to my son Shelah” (Gen. 38:26);“for because (כִּי עַל כֵּן) you passed by” (ibid. 18:5);“for because (כִּי עַל כֵּן) they came [under the shade of my roof]” (ibid. 19: 8);“for because (כִּי עַל כֵּן) I have seen your face” (ibid. 33:10).

You will be our guide: The verse has the past tense, [and] as the Targum renders, [it means: all the wonders wrought for us, you have seen with your eyes.] Another explanation: [It is in] the future tense-If anything should be hidden from our eyes, you shall enlighten us [with your guidance]. A further interpretation: You shall be as beloved to us as the pupils of our eyes, as it says, “You shall love the proselyte” (Deut. 10:9).

Then we will bestow on you the good: What good did they actually bestow upon him? They said, When Israel apportioned the Land, there was a fertile area of Jericho measuring five hundred by five hundred cubits, and they refrained from allocating it. They said, The one in whose portion the Temple will be built shall take it. Meanwhile, they gave it to the descendants of Jethro, to Jonadab the son of Rehab, as it says, “The sons of Keini, Moses’ father-in-law, went up from the city of dates [namely, Jericho]” (Jud. 1:16). - [from Sifrei]

The Ark of the Lord’s covenant traveled three days ahead of them: This was the Ark that accompanied them in battle. The broken pieces of the [first set of] Tablets lay in them. It preceded them by three days of travel to prepare for them a place to encamp. - [from Sifrei]

34The cloud of the Lord was above them by day, when they traveled from the camp.

לדוַֽעֲנַ֧ן יְהֹוָ֛ה עֲלֵיהֶ֖ם יוֹמָ֑ם בְּנָסְעָ֖ם מִן־הַמַּֽחֲנֶֽה:

The cloud of the Lord was above them: Seven clouds are recorded in the account of their travels: four from the four sides, one above, one below, and one in front of them which would flatten the high land, raise the hollows and destroy snakes and scorpions - [from Sifrei].